WO2014207389A1 - Use of a 2-octyl acrylate polymer as a binding agent in a coating composition - Google Patents
Use of a 2-octyl acrylate polymer as a binding agent in a coating composition Download PDFInfo
- Publication number
- WO2014207389A1 WO2014207389A1 PCT/FR2014/051615 FR2014051615W WO2014207389A1 WO 2014207389 A1 WO2014207389 A1 WO 2014207389A1 FR 2014051615 W FR2014051615 W FR 2014051615W WO 2014207389 A1 WO2014207389 A1 WO 2014207389A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- monomer
- use according
- weight
- ethylenically unsaturated
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
- C04B26/02—Macromolecular compounds
- C04B26/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C04B26/06—Acrylates
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B28/00—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements
- C04B28/24—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements containing alkyl, ammonium or metal silicates; containing silica sols
- C04B28/26—Silicates of the alkali metals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09D11/107—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/08—Homopolymers or copolymers of acrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
- C04B2111/00474—Uses not provided for elsewhere in C04B2111/00
- C04B2111/00482—Coating or impregnation materials
Definitions
- the present invention relates to the use of a polymer resulting from the polymerization of 2-octyl acrylate and optionally at least one other monomer, as a binding agent in or for the manufacture of a composition of coating.
- paint composition having the above-mentioned compromise of properties has been disclosed in application EP 0 599 676.
- This composition contains a polymer resulting from the polymerization of three distinct monomers, consisting in particular of a mixture of (meth) acrylic acid, a (meth) acrylic acid ester, such as n-butyl acrylate, and a benzophenone derivative, and optionally a fourth monomer which is styrene.
- Another type of paint composition has been described in US 2012/0121921.
- It is a flame-retardant and water-resistant polymer composition comprising a polymeric binder in latex form, obtained by radical polymerization of at least one ethylenically unsaturated monomer, especially comprising n-butyl acrylate, and tert-butyl (meth) acrylate.
- Acrylic compounds optionally associated with styrene, have the further advantage of allowing the formulation of paints with good resistance to light and weather conditions. However, they are usually produced from propylene, which is a by-product of petroleum refining. Oil deposits are running out quickly. To anticipate the supply difficulties related to these resources, it would be desirable to be able to substitute these acrylic compounds with compounds obtained from carbon sources of renewable origin.
- n-butyl acrylate does not contain sufficient carbon of renewable origin and that it has a more hydrophilic character than long-chain acrylates such as 2-octyl acrylate.
- the Applicant has demonstrated that it is possible to formulate a coating composition in film form, based on polymer of predominantly renewable origin, which composition has both good mechanical properties, and in particular a flexibility and elongation and a good cohesion, as well as a sufficiently hydrophobic character, using as a binder a homo- or copolymer based on 2-octyl acrylate.
- an acrylic resin based on 2-octyl acrylate and other (meth) acrylic monomers, prepared in an aqueous solvent is used as a barrier coating interposed between, on the one hand, a metallic substrate coated with a layer of paint obtained by electroplating, and secondly, an upper layer of paint.
- the acrylic resin has a glass transition temperature of -52 ° C and an elongation at break at -20 ° C of 610%.
- This coating is presented as flexible, adhesive, and above all capable of absorbing energy to protect the composite material against shocks, the latter advantageously constituting an automotive paint.
- the present invention thus relates to the use of a polymer resulting from the polymerization of 2-octyl acrylate of renewable origin and possibly at least one other monomer, as binding agent in or for the manufacture of a coating composition.
- coating is meant, in the present description, a layer applied to a substrate in film form, generally between 50 mm and a few mm thick, from a Tg-binding polymer of between -40 ° C. and + 40 ° C according to the law of Fox, said film being applied in a sufficient thickness to modify the appearance of the substrate, in particular its optical properties, and / or protect its surface, in particular against scratches, moisture, Dirt or light.
- coating composition therefore does not include adhesive compositions intended to improve adhesive properties of the substrate. On the other hand, it includes paint, mortar, coating, varnish and ink compositions, without this list being limiting.
- the polymer used according to the invention comprises 2-octyl acrylate of renewable origin.
- This monomer is mainly, or even entirely, derived from plant sources and can therefore be considered as a material of renewable origin, which is characterized by the fact that its content of 14 C represents at least 50%, preferably at least 60%, for example at least 70 ⁇ 6, or even at least 80%, that of atmospheric CO 2 (according to ASTM D6866).
- the 2-octyl acrylate contains at least 0.6 x 10 ⁇ 10 % by weight of 14 C relative to the total carbon, according to ASTM D6866-06.
- the 14 C content can be measured according to a liquid scintillation counting method and expressed as disintegrations per minute per gram of carbon, or dpm / gC.
- the dpm / gC value of the 2-octyl acrylate is generally at least 7.2 ⁇ 0.1 dpm / gC.
- the 2-octyl acrylate may be prepared from 2-octanol and acrylic acid, especially in the presence of an acid-type esterification catalyst comprising sulfur, such as methanesulfonic acid, and at least a polymerization inhibitor. Alternatively, it can be prepared by transesterification reaction between a light acrylate such as ethyl acrylate, and 2-octanol.
- the 2-octanol may itself be derived from the treatment of ricinoleic acid, derived from castor oil, with sodium hydroxide, followed by distillation to remove sebacic acid.
- a process for the preparation of 2-octyl acrylate by direct esterification is described in particular in application WO 2013/064775.
- the aforementioned monomer can be homopolymerized, in which case the polymer used according to the invention is a homopolymer of 2-octyl acrylate. As a variant, it may be copolymerized with at least one other monomer, so that the polymer used according to the invention is a copolymer containing, advantageously, from 1 to 80% by weight, preferably from 25 to 75% by weight, and more preferably 30 to 75%, or even 50 to 70% by weight, of 2-octyl acrylate, relative to the total weight of the copolymer.
- This other monomer can in particular be chosen from: vinylaromatic monomers, such as styrene; ethylenically unsaturated nitriles, such as
- esters of ethylenically unsaturated mono- and dicarboxylic acids such as 2-ethylhexyl acrylate, n-butyl acrylate and methyl methacrylate, itaconic acid esters
- esters of monocarboxylic acid and of vinyl or allylic alcohol such as vinyl acetate
- ethylenically unsaturated mono- and dicarboxylic and sulphonic acids such as (meth) acrylic acid, itaconic acid and styrene sulphonic acids
- ethylenically unsaturated mono- and dicarboxylic acid amides such as acrylamide
- N-vinyllactams such as N-vinyl pyrrolidone
- N-vinylamides such as N-vinyl pyrrolidone
- N-vinylamides such as N-vinyl pyrrolidone
- N-vinylamides such as N-vinyl pyrroli
- Preferred comonomers are ethylenically unsaturated mono and di-carboxylic acid esters, in particular methyl methacrylate and n-butyl acrylate, vinylaromatic monomers, more particularly styrene, and mixtures thereof.
- crosslinking monomers may be advantageously added to the 2-octyl acrylate before polymerization, in order to improve the chemical resistance properties to water or to various household products of the coating composition. These monomers can also improve the barrier or fouling resistance properties of the coating composition, or improve the mechanical properties of the polymer such as its resistance to elongation.
- crosslinking monomers non-limiting mention may be made of diacetone acrylamide in combination with adipic acid bishydrazide, hydroxylated monomers in combination with polyisocyanates, siloxane (meth) acrylates, and multifunctional (meth) acrylates. , that is to say having several unsaturations, and mixtures thereof.
- monomers functional non-exhaustively include acetoxyethyl (meth) acrylates, monomers carrying phosphate or phosphonate function (s), monomers bearing ureido function (s), monomers carrying amino function (s) and their mixtures.
- the monomers constituting the polymer used according to the invention can be polymerized in a conventional manner, for example by means of a radical polymerization in aqueous emulsion.
- the pH of the emulsion can be buffered to be maintained between 4 and 7 during the polymerization process.
- free-radical initiators those conventionally used in this type of reaction may be chosen, and in particular inorganic initiators such as ammonium, sodium and potassium persulfates, alone or in combination with a reducing agent intended to lower the polymerization temperature, or still organic initiators such as tert-butyl hydroperoxides or hydrogen activated by reducing agents.
- one or more chain transfer agent (s) may be added during the process to achieve the desired molecular weight distribution.
- the polymerization can be carried out at a temperature of 0 to 150 ° C, preferably 30 to 100 ° C and for example 50 to 90 ° C, for a period of 4 to 6 hours, for example. It can be conducted under atmospheric pressure and / or in the presence of an inert gas.
- This polymerization process results in a latex advantageously having a solids content of between 20 and 70% by weight and preferably between 35 and 60% by weight.
- the polymer obtained generally has a glass transition temperature (Tg), calculated using the Fox's law, of between -40 ° C. and + 40 ° C., preferably ranging from -30 ° C. to + 30 ° C., more preferably between -10 and 10 ° C, or between -10 and 0 ° C.
- Tg glass transition temperature
- the polymer can be obtained in a one-step process, that is to say with a continuous feed into a single monomeric composition, or in a multi-step process using different monomeric compositions, in order to obtain particles presenting different Tg domains.
- This type of particles is referred to as core-shell particles or structured particles.
- the average Tg of the polymers obtained at the end of each step may also be between -40 ° C. and + 40 ° C. and preferably ranging from -30 ° C. to + 30 ° C.
- the coating composition used according to the invention contains water. It may contain various additives chosen for example from: one or more pigments; one or more powdery fillers; one or more pH adjusters, in particular one or more bases, for neutralizing the acidic monomers optionally copolymerized with 2-octyl acrylate, such as an alkaline hydroxide (in particular sodium hydroxide), aqueous ammonia or a water-soluble amine; one or more dispersing and / or wetting agents, such as sodium, potassium or ammonium polyphosphates and naphthalene sulfonic acid salts; one or more thickeners, such as xanthan and cellulose derivatives; one or more anti-foam agents; one or several film-forming agents; one or more antifreeze agents; one or more flame retardants, especially organophosphorus compounds or magnesium or aluminum hydroxide; one or more biocides; and their mixtures.
- additives chosen for example from: one or more pigments; one or more powdery fillers; one
- the pigments may in particular be chosen from: white or colored inorganic pigments, such as titanium dioxide, zinc oxide, barium sulfate, antimony trioxide, iron oxides, ultramarine and carbon black; organic pigments, such as azo dyes, indigoids and anthraquinoids; and their mixtures.
- the pulverulent fillers may especially be chosen from: calcium or magnesium carbonate; silica; silicates, such as talc, kaolin, mica; calcium sulphate, aluminosilicates; and their mixtures. These charges are preferably implemented in finely divided form.
- the coating composition according to the invention may contain an additional binder, in particular a silicone resin or a silicate.
- the various constituents of the coating composition can be mixed in a conventional manner for those skilled in the art, in their usual proportions. It is preferred that the polymer is added, generally in the form of an aqueous dispersion (latex), in a dispersion or paste of pigments.
- the polymer in the form of an aqueous dispersion generally represents from 5 to 90% by weight, preferably from 10 to 75% by weight, relative to the total weight of the composition. In dry weight, the polymer generally represents from 5 to 50% by weight, and preferably from 20 to 40% by weight, relative to the total weight of the composition. This composition may be in liquid or semi-solid form.
- It preferably has a solids content of between 25 and 75% by weight and preferably between 35 and 65% by weight.
- composition used according to the invention can be applied to any substrate, especially wood, metal, glass, cement, paper, textile, leather, plastic or brick, by any means, including using a brush, a brush, a roller, a buffer, a spray or an aerosol, possibly after application to the substrate of an adhesion primer.
- this substrate It then forms on this substrate a film at room temperature ( ⁇ 30 ° C), to give it the desired aesthetic properties and to protect it, especially against moisture.
- the syntheses were carried out in a reactor of 3 1 (internal capacity) glass, equipped with a double jacket, equipped with an effective stirring (vortex), a refrigerant with triple flow, a control and a regulation of the material temperature.
- the reactor included the number of inlet connections necessary for the separate introduction of the various components, as well as an introduction dedicated to inerting. to the nitrogen of the whole. The tightness was checked before each synthesis.
- the installation was equipped with a system to adjust the introduction rates of the components. The temperature of the material, as well as the temperatures of the jacket, were recorded and adjusted. The synthesis was carried out semi-continuously.
- the solids content of the aqueous dispersions was measured according to the ISO 3251 standard.
- the pH of the aqueous dispersions was measured according to ISO 976.
- the viscosity of the aqueous dispersions was measured according to ISO 2555.
- Particle size was measured by Photon Correlation Spectroscopy (PCS), using Beckman Coulter N4 + apparatus.
- PCS Photon Correlation Spectroscopy
- the sample was diluted (3 to 5 drops of emulsion in 50 ml of water) in a polystyrene tank with deionized water on a 0.22 ⁇ cellulose acetate filter.
- the particle size was measured at a temperature of 25 ° C, a measurement angle of 90 ° and a laser wavelength of 633 nm.
- TMF Minimum film formation temperature
- Dispersion D1 A first polymer dispersion, hereinafter referred to as "Dispersion D1”, was prepared as follows.
- Emulsifier E30 15.25 g of a 40% solution of Emulsifier E30 were solubilized in 1165.85 g of demineralized water at the bottom of the tank.
- the pH of the bottom of the tank was advantageously less than 3.
- the temperature of the bottom of the tank was raised to 80 ° C.
- a pre-emulsion was prepared by dispersing 44.38g of Emulsifier E30 (40%) and 83.33g of Disponil FES 77 (30%) in 865.04g of deionized water with good agitation.
- the pre-emulsion thus formed was white and stable for at least the time of the polymerization. She was kept under slight agitation.
- the latex was neutralized by adding sodium hydroxide to pH 8-9 before adding a biocide. It was then adjusted to dry extract and filtered on 100mm canvas. The final dry extract amounted to
- a Dl dispersion comprising a MAM / A20ct / AA / Mallyl-based polymer was obtained in the mass proportions 40.3 / 58.5 / 1 / 0.2, with a Fox Tg of 0 ° C.
- the final particle size was about 130 nm, the viscosity was less than 1000 mPa.s, the measured TMF was 5 ° C.
- Example 2 Each dispersion obtained in Example 1, in film form, was applied to a polypropylene plate (800 ⁇ m hum) and dried for 7 days at 23 ° C. at 50% relative humidity.
- DMA Dynamic Mechanical Analysis
- Varnishes were formulated using the raw materials identified in Table 6 below.
- Example 1 The dispersions prepared in Example 1 were formulated as a varnish (35% solids content) having the following compositions: Varnish VI:
- the V3 varnish (formulated from the dispersion D4 which contains the bio-sourced A20CT monomer) has a water resistance equivalent to the Varnish VI which is formulated with the dispersion D2 containing no bioconomous monomer. source.
- Example 2 The mechanical tests as described in Example 2 were applied to these 3 dispersions, as well as tensile tests at 5 mm / min performed at -20 ° C.
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14/899,186 US9593191B2 (en) | 2013-06-28 | 2014-06-26 | Use of 2-octyl acrylate polymer as a binding agent in a coating composition |
CN201480036582.7A CN105324347B (en) | 2013-06-28 | 2014-06-26 | Purposes of the octyl group ester polymer of acrylic acid 2 as the adhesive in coating composition |
BR112015031262-4A BR112015031262B1 (en) | 2013-06-28 | 2014-06-26 | use of a 2-octyl acrylate polymer as a bonding agent in a coating composition |
MX2015017334A MX2015017334A (en) | 2013-06-28 | 2014-06-26 | Use of a 2-octyl acrylate polymer as a binding agent in a coating composition. |
KR1020167002203A KR20160025584A (en) | 2013-06-28 | 2014-06-26 | Use of a 2-octyl acrylate polymer as a binding agent in a coating composition |
EP14739897.8A EP3013767B1 (en) | 2013-06-28 | 2014-06-26 | Use of a 2-octyl acrylate polymer as a binding agent in a coating composition |
JP2016522704A JP6329258B2 (en) | 2013-06-28 | 2014-06-26 | Use of 2-octyl acrylate polymers as binders in coating compositions |
SG11201510604VA SG11201510604VA (en) | 2013-06-28 | 2014-06-26 | Use of a 2-octyl acrylate polymer as a binding agent in a coating composition |
ZA2015/08869A ZA201508869B (en) | 2013-06-28 | 2015-12-03 | Use of a 2-octyl acrylate polymer as a binding agent in a coating composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR13.56312 | 2013-06-28 | ||
FR1356312A FR3007767B1 (en) | 2013-06-28 | 2013-06-28 | USE OF A 2-OCTYL ACRYLATE POLYMER AS A BINDER AGENT IN A COATING COMPOSITION |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2014207389A1 true WO2014207389A1 (en) | 2014-12-31 |
Family
ID=49054833
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2014/051615 WO2014207389A1 (en) | 2013-06-28 | 2014-06-26 | Use of a 2-octyl acrylate polymer as a binding agent in a coating composition |
Country Status (12)
Country | Link |
---|---|
US (1) | US9593191B2 (en) |
EP (1) | EP3013767B1 (en) |
JP (1) | JP6329258B2 (en) |
KR (1) | KR20160025584A (en) |
CN (1) | CN105324347B (en) |
BR (1) | BR112015031262B1 (en) |
FR (1) | FR3007767B1 (en) |
MX (1) | MX2015017334A (en) |
MY (1) | MY179975A (en) |
SG (1) | SG11201510604VA (en) |
WO (1) | WO2014207389A1 (en) |
ZA (1) | ZA201508869B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107406557A (en) * | 2015-02-13 | 2017-11-28 | 帝斯曼知识产权资产管理有限公司 | Aqueous polymer emulsion |
US10662273B2 (en) | 2016-12-19 | 2020-05-26 | Celanese International Corporation | Waterborne acrylic dispersions with high biorenewable content |
WO2023148332A1 (en) | 2022-02-04 | 2023-08-10 | Basf Se | Polymer binder based on 2-octyl acrylate, n-butyl acrylate and methyl methacrylate for aqueous coating compositions containing titanium dioxide |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109563369A (en) * | 2016-07-04 | 2019-04-02 | 帝斯曼知识产权资产管理有限公司 | Aqueous polymer emulsion |
KR20230048632A (en) | 2020-08-14 | 2023-04-11 | 테사 소시에타스 유로파에아 | pressure sensitive adhesive composition |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4983454A (en) * | 1985-09-17 | 1991-01-08 | Kansai Paint Co., Ltd. | Process for coating metallic substrate |
WO2009129087A1 (en) * | 2008-04-14 | 2009-10-22 | 3M Innovative Properties Company | 2-octyl (meth)acrylate adhesive composition |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2697530B1 (en) | 1992-11-04 | 1994-12-16 | Rhone Poulenc Chimie | Binder for paint based on acrylic latex or styrene / acrylate. |
JPH09279064A (en) * | 1996-04-12 | 1997-10-28 | Honny Chem Ind Co Ltd | Water-soluble resin composition |
JPH10231325A (en) * | 1997-02-17 | 1998-09-02 | Daicel Chem Ind Ltd | Acrylic polymer and resin composition containing the same polymer |
JP2000280419A (en) * | 1999-03-31 | 2000-10-10 | Dainippon Printing Co Ltd | Decorative sheet and op coating agent for polyolefinic decorative sheet |
US7385020B2 (en) | 2006-10-13 | 2008-06-10 | 3M Innovative Properties Company | 2-octyl (meth)acrylate adhesive composition |
EP2094794B1 (en) * | 2006-12-04 | 2010-06-23 | E.I. Du Pont De Nemours And Company | Acrylic polyol coating composition |
ITRA20070041A1 (en) | 2007-05-24 | 2008-11-25 | Piercarlo Molta | METHOD AND PLANT FOR THE PRODUCTION OF MEMBRANE BODIES |
JP2011508804A (en) | 2007-12-18 | 2011-03-17 | スリーエム イノベイティブ プロパティズ カンパニー | Fine particle pressure sensitive adhesive composition |
US20120329898A1 (en) | 2008-04-14 | 2012-12-27 | 3M Innovative Properties Company | 2-octyl (meth)acrylate adhesive composition |
JP2011518921A (en) | 2008-04-23 | 2011-06-30 | スリーエム イノベイティブ プロパティズ カンパニー | Microsphere pressure-sensitive adhesive composition |
ES2562528T3 (en) | 2009-07-22 | 2016-03-04 | Basf Se | Aqueous polymer dispersions as binders for plasters and paints with improved fire behavior |
US8067504B2 (en) * | 2009-08-25 | 2011-11-29 | 3M Innovative Properties Company | Acrylic pressure-sensitive adhesives with acylaziridine crosslinking agents |
FR2964970B1 (en) | 2010-09-22 | 2013-11-01 | Arkema France | NEW MODIFYING SHOCKS AND IMPROVED THERMOPLASTIC COMPOSITIONS SHOCK |
EP2655508B2 (en) | 2010-12-20 | 2021-04-14 | DSM IP Assets B.V. | Bio-renewable sequential vinyl polymer |
-
2013
- 2013-06-28 FR FR1356312A patent/FR3007767B1/en active Active
-
2014
- 2014-06-26 SG SG11201510604VA patent/SG11201510604VA/en unknown
- 2014-06-26 BR BR112015031262-4A patent/BR112015031262B1/en active IP Right Grant
- 2014-06-26 JP JP2016522704A patent/JP6329258B2/en active Active
- 2014-06-26 US US14/899,186 patent/US9593191B2/en active Active
- 2014-06-26 EP EP14739897.8A patent/EP3013767B1/en active Active
- 2014-06-26 WO PCT/FR2014/051615 patent/WO2014207389A1/en active Application Filing
- 2014-06-26 MY MYPI2015003027A patent/MY179975A/en unknown
- 2014-06-26 KR KR1020167002203A patent/KR20160025584A/en not_active Application Discontinuation
- 2014-06-26 CN CN201480036582.7A patent/CN105324347B/en active Active
- 2014-06-26 MX MX2015017334A patent/MX2015017334A/en unknown
-
2015
- 2015-12-03 ZA ZA2015/08869A patent/ZA201508869B/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4983454A (en) * | 1985-09-17 | 1991-01-08 | Kansai Paint Co., Ltd. | Process for coating metallic substrate |
WO2009129087A1 (en) * | 2008-04-14 | 2009-10-22 | 3M Innovative Properties Company | 2-octyl (meth)acrylate adhesive composition |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107406557A (en) * | 2015-02-13 | 2017-11-28 | 帝斯曼知识产权资产管理有限公司 | Aqueous polymer emulsion |
US10662273B2 (en) | 2016-12-19 | 2020-05-26 | Celanese International Corporation | Waterborne acrylic dispersions with high biorenewable content |
EP3555217B1 (en) | 2016-12-19 | 2021-02-17 | Celanese International Corporation | Waterborne acrylic dispersions with high biorenewable content |
WO2023148332A1 (en) | 2022-02-04 | 2023-08-10 | Basf Se | Polymer binder based on 2-octyl acrylate, n-butyl acrylate and methyl methacrylate for aqueous coating compositions containing titanium dioxide |
Also Published As
Publication number | Publication date |
---|---|
CN105324347A (en) | 2016-02-10 |
EP3013767A1 (en) | 2016-05-04 |
BR112015031262B1 (en) | 2021-03-16 |
FR3007767A1 (en) | 2015-01-02 |
JP6329258B2 (en) | 2018-05-23 |
EP3013767B1 (en) | 2018-05-30 |
JP2016524020A (en) | 2016-08-12 |
FR3007767B1 (en) | 2016-05-27 |
KR20160025584A (en) | 2016-03-08 |
US20160152751A1 (en) | 2016-06-02 |
CN105324347B (en) | 2018-03-30 |
BR112015031262A2 (en) | 2017-07-25 |
ZA201508869B (en) | 2017-11-29 |
MY179975A (en) | 2020-11-19 |
SG11201510604VA (en) | 2016-01-28 |
MX2015017334A (en) | 2016-04-06 |
US9593191B2 (en) | 2017-03-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2222717B1 (en) | Polymer aqueous dispersion with core/skin structure, method for making same and application thereof in coatings | |
EP2456791B2 (en) | Aqueous self-crosslinkable polymer dispersion made from hard-core, soft-shell structured polymer particles, and coating or treatment compositions | |
EP3013767B1 (en) | Use of a 2-octyl acrylate polymer as a binding agent in a coating composition | |
EP3068814B1 (en) | Aqueous dispersion of polymer made from multistructured particles for aqueous coatings having improved blocking and fingerprint resistance and hardness | |
FR2897870A1 (en) | Aqueous polymer nanocomposite dispersion, useful e.g. in coating composition, particularly protective coating composition e.g. as varnishes, comprises polymerized product of monomers and an aqueous dispersion of silica nanoparticles | |
KR101717073B1 (en) | Fluoropolymer aqueous hybrid compositions with improved film formation | |
EP1725595A1 (en) | Polymer aqueous dispersion for a barrier coating | |
TW200936614A (en) | Emulsion polymers, aqueous dispersions and processes for preparing them | |
FR2889989A1 (en) | Use of aqueous dispersion in surface treatment of wood, where dispersion comprises latex made of polymerization of monomer mixture emulsion comprising monomers e.g. butadiene, and another monomers like (meth)acrylic having ureido groups | |
EP0728154B1 (en) | Aqueous polymer dispersion, method for making same, and use thereof for preparing paints | |
EP0653469A2 (en) | Aqueous coating compositions based on room-temperature crosslinking latex | |
FR2540880A1 (en) | LIME DISPERSION PAINT AND PROCESS FOR PREPARING THE SAME | |
FR2806089A1 (en) | Use of polymer based on imido-maleic anhydride as agent inhibiting surface migration and/or providing a water-/alkali- resistant coating in surface treatment, surface-protective and coating compositions and in inks and varnishes | |
WO2007012432A1 (en) | Structured polymer based aqueous dispersion, method for obtaining same and uses thereof in formulations for paints | |
FR3030530A1 (en) | COPOLYMER DIBLOC WATER SOLUBLE | |
EP3068815B1 (en) | Aqueous dispersion of polymer made from multistructured particles for aqueous wall coatings resistant to dirt and wet abrasion | |
EP3374439B1 (en) | Coatings having an improved stain and dirt resistance | |
EP1451236B1 (en) | High-washability aqueous polymer dispersion, preparation and use thereof as binder in coating compositions | |
FR2526033A1 (en) | Water-repellent compsns. - contain film-forming alkyl acrylate!-vinyl! aromatic copolymer and alkali alkyl-siliconate | |
FR2804369A1 (en) | MULTI-LAYER COMPOSITE PRODUCT WITH A PRESSURE-SENSITIVE AND TEMPERATURE-RESISTANT ADHESIVE POLYMER LAYER | |
FR2824081A1 (en) | COMPOSITIONS FOR ANTI-CORROSION TREATMENT OF METALS CONTAINING AQUEOUS POLYMER DISPERSIONS, FILMOGENOUS IN THE ABSENCE OF ORGANIC SOLVENT |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 201480036582.7 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 14739897 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2014739897 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: MX/A/2015/017334 Country of ref document: MX |
|
WWE | Wipo information: entry into national phase |
Ref document number: 14899186 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: 2016522704 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: IDP00201508789 Country of ref document: ID |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112015031262 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 20167002203 Country of ref document: KR Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 112015031262 Country of ref document: BR Kind code of ref document: A2 Effective date: 20151214 |